1-Methylpiperazine → 2-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

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Reaction Steps

To a solution 0.18 g (0.41 mmole) of 2-(5-formyl-2-nitro-phenylamino)-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17b) and 0.18 g (0.83 mmole) of sodium triacetoxy-borohydride in 15 mL of dichloromethane was added 0.069 mL (0.62 mmole) of 1-methylpiperazine. The mixture was stirred at room temperature overnight. The mixture was then diluted with dichloromethane, washed with saturated sodium bicarbonate, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with dichloromethane-methanol (gradient 100:0-75:25) gave 0.16 g of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.17c) as a yellow solid.

Provenance & Evidence